


They were the Best of Times

by Pineapplemoon



Series: I'm a Book Half Unread [16]
Category: Gilmore Girls
Genre: Emotional Hurt/Comfort, Family, Father-Son Relationship, Gen, Humor, Post-Break Up, Sibling like relationship
Language: English
Status: In-Progress
Published: 2019-12-23
Updated: 2020-01-21
Packaged: 2021-02-26 18:54:48
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 12,529
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21913387
Author URL: https://archiveofourown.org/users/Pineapplemoon/pseuds/Pineapplemoon
Summary: Break ups, mysterious letters, and forced speech giving, Jess just wants this school year to be over.
Relationships: Lorelai Gilmore & Jess Mariano, Luke Danes & Jess Mariano, Post Jess Mariano/Original Male Character, Richard Gilmore & Jess Mariano, Rory Gilmore & Jess Mariano
Series: I'm a Book Half Unread [16]
Series URL: https://archiveofourown.org/series/1077063
Comments: 36
Kudos: 76





	1. Chapter 1

**Author's Note:**

> This is most likely going to be three parts in total, so buckle up for a wild ride as high school comes to an end for Jess and the gang.

The next morning, Rory joins her mom to Luke’s, both of them worried about Jess. Right after Rory made sure Lane got home safely last night, she went straight home to tell her mom everything that happened. She was devastated, but glad that Jess did the right thing driving Oliver home and that Dean was there to give him a ride back to Stars Hollow. She sent Rory to bed, not knowing that Rory listened at her door as she called Luke to give him a heads up. 

“That was one wild party you went to last night.” Lorelai comments as they pass Kyle’s house, where him and a friend clean up trash left in the yard, Kyle’s parents watching in silent anger from the porch.

“The wildest.” Rory sighs. “I just feel so bad for Jess and Lane. They were the two most looking forward to this party and they both had a terrible time.”

“I know, baby.” Lorelai pets her hair. “You’re a good friend, you know that?”

“I guess…”

“Trust me, you cross the line into good friend once you hold your friend’s hair back as she pukes in someone’s yard.”

Rory cracks a smile. “Is that in the official friend guideline booklet?”

“Yup, right above letting them have the good snacks that you usually hide when people come over.” Lorelai holds the door open, letting Rory in first. 

Luke spots them right away and comes straight to them as they sit at the counter. 

“How’s Jess doing?” Her mom asks first thing.

Luke shakes his head. “I have no idea. He got home late after being out with Dean, which Dean came and collaborated this morning, went straight to bed, and was still sleeping when I got up to come open up down here.” Right as Luke finished his list, they heard a thump from upstairs.

“Well, it sounds like he’s up now.”

“I can go check on him.” Rory volunteers. “I just mean, after my breakup with Dean, the last thing I wanted to do was talk about it with grownups. No offence.” She tacks on at the end.

Both adults shake their heads. “None taken.” Her mom speaks for both of them. 

“I think that’s a great idea. Thank you, Rory.” Luke says, looking like a huge weight was lifted off his shoulders.

With one last nod and smile, Rory ducks out and up the stairs, knocking on the door. “It’s just me.” She adds through the door.

Jess opens the door, hair a wild mess and still in his pajamas. He moves to the side to let her in. “How many know?” He asks after shutting the door.

Rory winces. “At this point, just about the whole town. I’m sorry.” In the corner of her eye, she notices a pile of stuff by the door.

Jess shrugs. “Doesn’t matter.” Going to his side of the room, he starts digging through a pile of stuff on his bed, finding certain things and throwing them into the pile by the door. She stands silently as he tosses a cassette tape, some old vhs tape, and a book of Tale of Two Cities. When he grabs the stuffed bear from the winter carnival and tosses that too, she figures this is her cue to step in.

“What are you doing?”

He pauses, looking up. “What does it look like? I’m getting rid of all this crap.”

She picks up the bear, holding it close. “Even Theodore? You love this bear.”

Jess marches over, snatching it from her and tossing it to the ground. “No, I don’t. It’s just a stupid stuffed animal.” He goes back over to his bed, this time keeping his back to her.

Rory bites her lip, knowing exactly what he’s doing now, having done the same thing after her and Dean broke up the first time. “And the book? I  _ know _ you like that book, you read it all the time.”

“Look at the title page.” Is all he says.

Kneeling down, she flips the book open to the front page, seeing what he means. In familiar blocky handwriting is Oliver’s name, along with his number and a little smiley face. Sighing, she sets the book back down and picks up the movie, turning it over to see it’s the one Oliver had gotten him as a belated Christmas present. When she asked Jess later what  _ Mac and Me _ meant, Jess only said it was an inside joke between him and Oliver. The tape she recognizes as the one that was stuck in his car. She’s sure that has some meaning too, but doesn’t want to hurt him more by asking.

“Are you sure you want to get rid of this stuff so soon?” She asks softly, standing back up. “I know you’re hurting and want it gone, but-”

“I’m not hurting.” He cuts her off curtly. “I’m fine, I just don’t want this crap cluttering up what little space we have up here. Speaking of,” Going into his closet, he pulls out a Chilton uniform, handing it to her. “Can you give this back Monday?  _ I _ certainly don’t need it.”

“Um, sure. Of course.” She takes the uniform, folding it in half and setting it on the one of the dining chairs. 

“How did the rest of the party go? Did Lane’s band feel more relaxed playing their second set?” Jess asks, obviously trying to change the subject.

“They didn’t.” Jess gives her a strange look. “Oliver wasn’t the only one that had too much to drink. Lane got wasted and I had to take her home. Turns out it didn’t matter, as we were leaving the cops showed up about a noise complaint and broke up the party.

“That’s too bad.” He goes back to throwing more stuff.

Rory watches him, trying to think what her mom would do. “Jess, please stop. I really think you should wait until you’ve had time to process everything-”

“Would you quit it! I told you I’m fine!” He snaps, spinning around, and with more force than necessary, lobs a CD at the pile where his cat is investigating. With a squawk of surprise, Billy just narrowly misses getting hit, darting to safety under Luke’s bed.

Rory glares at him for that. He drops his anger, looking guilty for that. “I didn’t mean-”

“I get it, you broke up with someone last night, and despite what you say, I  _ know _ you’re not over it, but you need to stop before you do something you’re going to truly regret.” Rory talks over him, done trying to coddle him.

“I know, but every time I look at this stuff it hurts! I wake up, feeling slightly better than when I went to bed, but then I turn and see another reminder of him and everything floods back to me and then I go right back to feeling like something died in me and-”

Rory, noticing him start to spiral, grabs his shoulders and guides him to sit on the couch. “Hey, slow down. Things will get better, I promise. But first things first, do you have an empty box and a sharpie?”

00000000000000000

Jess manages to make it through the weekend, working more at the inn and less at Luke’s. Lorelai needed the extra help since she had to lay off most of the workforce after the fire, and staying around in the open at Luke’s with all the townies asking, “How he’s doing?” was driving him completely insane. If he has one more person he barely knows come up to him and tell him that, “There are more fish in the sea.” then he is not accountable for his actions.

Rory was the biggest help. She had him put everything that reminded him of Oliver into a box and stick it to the back of his closet. A part of him wishes he had done that with all the stuff that reminded him of Liz, but he was stupid and had burned all of it the night before he moved here. Now the only photos of him as a kid that exist are the ones that Luke’s been holding on to. Even Luke doesn’t know that he got rid of them, he just made an excuse that they must have gotten lost in the many moves him and Liz went through. Luke, knowing how much of an airhead Liz can be, bought it immediately, shaking his head that it was a shame.

School on Monday is a different story. Where the older population of Stars Hollow would console him, the teenage population just watches from a distance. Every time he enters a room a hush falls over everyone, and a few send him apologetic looks. He is officially over all of this. He just wants everything to go back to normal

That doesn’t seem to be the case any time soon though. As he enters homeroom, the teacher hands him a note from the office, an excited look on her face.

“Congratulations, Jess. I knew if you put the effort in you could do it.”

Jess blinks at her, taking the note. “Okay…?” He flips the note open as he heads for his seat, more than curious on what all the fuss is about. It looks official, printed on the ‘nice’ paper, and starts with ‘Congratulations…’ He skims past all the mushy crap that talks about how great his grades and test scores are and that he’s an active member of the ‘school community’ until he gets to the main part, which reads that after much consideration, they are proud to name him the valedictorian for the class of 2003.

Spinning around, he heads for the door, making a quick excuse that he needs to use the bathroom to the teacher in passing.

It has to be some mistake. There is no way they are making  _ him _ valedictorian. He hates this place. If it wasn’t for Luke, he wouldn’t even  _ be _ here ninety percent of the time. This isn’t him. He isn’t some nerd that battled for the top like Paris. He doesn’t want this, and he’s going to make sure this damn school knows it.

Marching straight to the office, he bypasses the secretary outside, despite her trying to stop him, and heads straight into the principal's office.

“Hell no.”

The principal sighs, setting down his pen. “Mr. Mariano, a pleasure as always.”

“I’m sorry, sir, I tried to stop him, but-”

“It’s fine, Mary, I was expecting this. This is why I had you clear my morning.”

The secretary huffs, glaring at Jess as she leaves and shuts the door behind her.

“Jess, take a seat.” The principal gestures to the chair across from his desk.

Jess stays standing out of protest. “I don’t want this.” He holds the letter up.

The principal leans back in his chair, taking his glasses off. “So you’ve said.”

“Why me? You knew I’d hate this, so why the hell did you pick me?”

“Because, as we put in the letter, you have the highest test scores this school has ever seen. You are the only student we’ve ever had get accepted into all of the Ivy league schools, and you are well liked on top of it, most of the time anyway. We would be idiots  _ not _ to pick you. Now, unless there is a legitimate reason you think you shouldn’t be valedictorian, aside from ‘You don’t want to’, then please tell me and we’ll award this honor to someone else.”

Jess stands there speechless, trying to come up with a good argument, but comes up blank. Out of steam, he collapses in the chair that was pointed out to him earlier. “I cannot  _ wait _ until I’m done with this place.” He grumbles.

“Now, there’s something we can agree on.” The principal shakes his head with a chuckle. “You know, in my seven years of doing this job, never have I had a student come and complain because they  _ get _ to be valedictorian."

Jess sends him a sardonic smile. "You know me, I love keeping you on your toes."

“And you’ve been extremely successful in your endeavor. Now, if you’re finished pouting, I believe your next class is about to begin.” The principal returns his focus to whatever he was doing before Jess barged in.

“If I start skipping now, think I’ll have enough absences added up so I don’t have to be valedictorian?” Jess tries one more time as he stands.

The principal glances up from his paperwork. “This conversation was a pleasure as always, Mr. Mariano. Oh, and don’t forget to write a speech for graduation. It should be about ten minutes in length.”

Jess rolls his eyes, heading for the door. “I don’t know why I try with you anymore.”

“This is a family event, so keep it clean! If you wouldn’t say it in front of your grandmother, you’re not saying it on the podium.” He calls out as Jess leaves.

Jess waves that he heard. “Yeah, yeah, it’ll be a regular after school special.” He hears laughter as he closes the door. The secretary shoots him another dirty look, which he returns. 

00000000000000000

After school, he drops his bag off at home, dodging what has become the usual condolences, and tells Luke in passing that he’s off to meet Rory at her place. Luke nods in understanding and lets him go without a fight. If there is one good thing that came out of this breakup, it’s been Luke letting him off the hook from work.

Knowing Rory still has about an hour bus ride, he makes himself comfortable on a bench, pulling out his book. The hour passes by swiftly, and before he knows it Rory appears in front of him.

“This is a surprise.” She comments after making sure she has his attention away from his book.

“Long day at school. I just needed to get away for awhile.” He says as he stands and slips his book into his back pocket.

She winces. “People acting weird around you because of the breakup?”

Jess groans. “I wouldn’t be surprised if you told me they were all replaced with pod people. I thought it would at least die down at Luke’s by now, but even they’re still being weird. Taylor was  _ nice _ to me. I draw the line at Taylor taking pity on me.”

“How nice are we talking? The biting back rude comments to you nice or smiling at you nice?”

“He asked me how my day was.”

Rory’s eyes widen. “He was small talk nice? He wasn’t even that nice to me after Dean and I broke up. No wonder you wanted to get away.” 

“Anyway, I’ve had enough talking about me, how’s jolly good chilton? Paris driving you crazy yet about the final issue of the paper?”

It’s Rory’s turn to groan, which Jess takes a little delight in. “Like you wouldn’t believe. This is the closest I’ve ever seen her to actually wringing Madline and Luise’s necks for slacking.” She hesitates about the next part. “Another thing happened, but I’m not sure you want to hear it. It’s about Oliver.”

Jess pushes down his instinct to freeze, trying to remind himself not to flinch every time he hears his name. “Was there a problem when you tried to return his uniform? If he said something to you, I want you to remind him that his issue is with me, not you. You had nothing to do with us.”

She shakes her head. “No, nothing like that. The problem was with Paris. She wanted to know why I had a male uniform with me, and when I told her what happened Friday night, she tried to fire Oliver.”

Jess stops in his tracks. “What?!”

“She can’t.” She corrects quickly. “Only our adviser can have someone removed and she shut Paris down in no time.”

“But why? Paris, I wouldn’t say hates me, but she doesn’t exactly like me.”

“Well, she tried to use the bases that it would look badly on both Chilton and the paper if one of our writers were found drunk at a party, but I think it’s because she’s finally warming up to you in her own Paris-ey way. She told me later that she’s enjoyed going head to head against someone who’s read almost as much as her.”

Jess snorts at ‘almost’. “That’s only because unlike Paris, I actually have a life outside of school and reading.”

Rory lets out a sarcastic laugh. “Really now? And how long were you reading on that bench before I showed up?”

Jess glares at her. “I plead the fifth.”

“That’s what I thought.”

0000000000000000000

Once they get to the house, they split off in the hallway. Rory goes to her room to change out of her uniform, and Jess heads into the living room and collapses on the couch next to Lorelai who is going through a box of clothes.

She doesn’t flinch at his dramatic entrance, not looking away from a skirt she’s holding up.

Not getting the reaction he thought he would, Jess groans.

“Your casper audition is going along great there.”

Jess flips onto his back, giving her a look. “Can we just skip the whole ‘I pretend that I don’t want to talk about something when really I do, I’m just waiting for you to push a little’ interaction, and go straight to the part where I tell you how sucky this day was?”

Lorelai sets the skirt off to the side and sits on the edge of the coffee table, giving him her full attention. “What happened?”

With a sigh, Jess sits up and grabs his bag, digging through it until he finds the stupid letter that ruined his day. Not wanting to see her reaction, he hands the letter to her then flops back down onto the couch, covering his eyes with his arm.

After a moment of reading, she grabs the closest part of him to her, which is his leg, and gasps. “Oh my god.”

“I know, that whole stupid school is on crack or something.”

She ignores him, repeating ‘oh my god’ again, only louder this time. That seems to get Rory’s attention, who bolts out of her room and into the living room. “What’s going on? Is someone hurt?”

Jess moves his arm out of the way slightly and peeks his eyes open in time to watch Lorelai shoot up, handing Rory the letter. 

After a minute Rory’s head shoots up. “Oh my god!”

“Find a new sentence please!” Jess snaps. “You two are like a freaking record that keeps skipping!”

“Why didn’t you tell me about this earlier?” Rory asks, excitement clear on her face. “This is incredible!”

“When, two minutes ago? I just found out this morning. Sorry I waited the whole walk back from the bus stop.”

Rory wrinkles her brow at his tone. “Wait, you don’t sound happy. Why aren’t you happy about this?”

“Yeah, you told me this day was sucky. This is the opposite of sucky in my book.” Lorelai chimes in.

Jess sits up, rolling his eyes and running a hand through his hair nervously. “Because, I never wanted this. I never even tried. I know people were battling it out for this stupid title at school, and yet it was just handed to me when I did nothing to deserve it. The school won’t even let me back out, I talked to the principal and everything.”

Lorelai sighs, taking a seat next to him. “Oh, kid, we have got to work on this low self-esteem thing you have going on. Look at your grades and all the shiny acceptance letters you got, you completely earned that title, no doubt about it. What makes you think you didn’t earn it?”

Jess shrugs, not sure himself. He just knows it feels wrong.

Lorelai rubs his back. “Well I think, with all the extra work you had to put in in just one year to get your grades up from failing to all A’s that you more than deserve the title of valedictorian.”

Jess only shrugs again, nothing left to say. He wants to believe everything Lorelai is saying, but he doesn’t know how to word it in a way that she’ll understand. Rory must notice that his mood is still off, because she plops down on the other side of him. “I’m going to Grandma and Grandpa’s for a movie night tonight, want to tag along, get away from the Hollow for a bit?”

“Oh god, yes.” Jess gets up, eager to get out of this prison of a town for a few hours.

“You kids have fun.” Lorelai says from her place on the couch. “My keys are in my purse, so whoever finds it first gets to drive.”

Rory runs off in search of the purse, Jess turning around instead. “You’re not going too?”

Lorelai gives a very obvious fake smile. “Nah, I have a lot to do, and I chatted on the phone with her earlier and got all caught up.”

“Huh.”

She squints, tossing an old skirt at him that he easily bats out of the way. “Don’t ‘huh’ me, mister. I have a life outside of visiting my mother. Now, if you want those keys, I think I remember putting my purse somewhere upstairs. You can still beat Rory if you hurry.”

Jess stares at her, knowing she’s just trying to get him to drop it, but decides to let it go for now. “Can you drop my bag off at Luke’s? And let him know I’ll be gone for dinner?” He asks as he starts up the stairs.

Lorelai rolls her eyes, just as quickly back in a playful mood. “Fine, but it’ll cost you.” She says in a weary way.

“Just add it to my tab!”

000000000000000000000000

Lorelai lugs Jess’ bag to Luke’s, dumping it behind the curtain for him before sitting at the counter. Without being asked, Luke pauses from sorting the mail and pours her a cup of coffee.

“What else you want?”

Lorelai sets her mug down after taking a sip. “Wow, with such wonderful customer service like that, no wonder this place is packed.” She gestures to the empty restaurant.

Luke rolls his eyes, leaning forward on the counter. “It’s the midafternoon lull. Post after school and lunch crowd, but before the dinner crowd. You know I like to use this lull to get through my mail so I don’t have to do it nine at night.”

“Yeah, but your sign says open, not the illusion of open while I sort my mail.”

“Order your food, or I’ll switch that sign to closed and you can find somewhere else to eat.”

Lorelai pouts, able to tell she can’t keep this up much longer. “Fine, burger and fries.”

Luke nods, pushing back from the counter so he can tell Caesar the order. “Thank you.”

When he returns, Lorelai starts speaking again. “Jess and Rory are having a movie night with my parents, hence why I played pack mule.”

“Thanks for letting me know.” He keeps his head down, flipping through envelopes.

Lorelai debates telling him the other news she learned today. On the one hand, it was telling that Jess trusted her enough to let her know something was bothering him all on his own. But if she talks to Luke about it, then Jess might not be as willing to open up to her in the future. On the other hand, if she were in Luke’s shoes, she would absolutely want someone to tell her if Rory told them something.

“Jess told me something today.” She blurts out. Luke sighs at the interruption again, setting down his mail and looking at her. “He’s the class valedictorian.”

“I know.”

Lorelai’s jaw drops. “You know? How? Did he tell you?”

“Nope. His school called. They seemed to have finally realized that Jess isn’t the most reliable messenger and that his notes from school seem to ‘get lost’ in transit.”

Lorelai blinks, confused as to why he isn’t reacting more…  _ anything. _ “Well? You don’t seem very concerned that he’s keeping such a huge thing from you.”

Luke shrugs. “I’m giving him time. If he decides he wants to tell me, great. If not, well, even he knows I’m going to find out eventually. Him being introduced at his graduation as valedictorian and giving a speech are two pretty big giveaways.”

“That’s… actually a pretty good way of thinking about it.”

“Plus,” Luke adds. “If he doesn’t tell me, and I ‘find out’ at his graduation, then I get to use that to my advantage later on. I will hang that over that kid’s head for  _ so _ long.”

“Ah, there it is.” 

Luke hands her her food from the kitchen. She enjoys the meal in silence, Luke getting back to sorting his mail and her glad to have that secret off her chest.

A few minutes into the burger, Luke swears, tossing down an envelope. 

“What’s wrong?” She asks, wiping her hands on her napkin.

With nothing to say, Luke slides the envelope to her. It’s addressed to Jess, which isn’t too weird, he gets mail too. Then she looks at the return address in the corner that has the name Jimmy Mariano. “Oh.”

“Yup.” Luke says sarcastically. “Damn it! Just when you think he’s gone, he needs to pop back up!” Exhaling sharply to calm down some, Luke starts again. “What do you think he wants?”

“I don’t know.”

“What if he wants to see Jess? The last time that jerk showed up, Jess spiraled. He’s in a good place. I mean, I know he had that bad break up, but overall he’s doing better. That might go all out the window if he randomly decides he wants to waltz back into Jess’ life.” Luke pauses, looking back up at her. “I have to tell him about this, don’t I?”

Lorelai nods reluctantly. “Unfortunately. This is a little bit bigger than Jess keeping the fact that he’s valedictorian from you.”

Luke hangs his head. “Yeah, I figured as much.”

00000000000000000000000

Since Jess won the race to find the keys, he got to drive the jeep into Hartford, but unfortunately had to surrender the driving rights to Rory on the way back that evening. He was surprised by how much fun he ended up having at the Gilmore movie night. Rory was only able to keep the secret of him being valedictorian to herself for a grand total of two minutes, blurting it out mid conversation before they even got their coats off. 

Do to the great news, they found it fitting to let him choose the movie for tonight. Not expecting much, he was shocked when Emily had a couple maids bring out boxes full of movies,  _ good _ movies at that. Ranging from  _ Nosferatu _ to  _ Citizen Kane _ to  _ Gone with the Wind, _ they had it all. Rory got down on her knees to look through the movies with him, commenting on some of them. 

Emily wasn’t sure ‘what movies kids are into these days’, so she just ordered someone to ‘get whatever is the most popular ones from over the years’. She then not-so-subtly mentions that if there is more than one movie that they want to see, that they are always welcome over to do another movie night, maybe on Friday nights… 

Wanting to move past the awkwardness, Jess grabs a movie he figures would work for everyone, Alfred Hitchcock’s  _ Rear Window. _

Figuring they would go upstairs to watch it, both him and Rory are surprised when they find a projector set up in the sitting room, along with asking them what ‘flavored popcorn’ they would like. The whole thing was so transparent, even Richard was cringing at some of the things Emily had planned.

The icing on the cake of the whole evening was at the end though, when Emily gave Rory an extra bag of caramel corn and told her to give it to her mom so that she would, “Have a taste of what she missed out on.”.

By the time they got on the road, they couldn’t help it anymore and burst out laughing. Getting control over his breathing, Jess wipes a tear from his eye. “Okay, was it just me, or was that simultaneously the best  _ and _ worst night ever in the history of Gilmore dinners?”

“Grandma let us eat in the  _ lounge, _ with  _ tv trays. _ I’ve never eaten in a room that wasn’t the dining room or kitchen ever in my life in that house.”

“Forget the room, I never thought I’d see Emily serve  _ cheeseburgers _ with a straight face. Don’t get me wrong, they were the fanciest cheeseburgers I’ve had in my life, but they were still  _ cheeseburgers _ by the person who has said on multiple occasions that a proper meal is one that you eat with cutlery, not your hands like some wild beast.”

Rory laughs at that, nodding in agreement. “And the movies! What did she do, buy a whole movie store?”

“You joke, but knowing your grandmother, that is entirely within reason. Frankly, I’m surprised she didn’t rent out a private theater.”

Rory shakes her head with a grin, focusing back on driving.

Jess lets silence fall over the car for a while, knowing he should thank her for being a buffer for the night. He had forgotten that Emily is in the DAR with Oliver’s grandma, and of course word reached her about the nasty breakup. As soon as Emily brought it up, Rory jumped in and quickly changed the subject. Emily caught on, letting the subject shift without any complaint. “Thanks. For playing interference on the you-know-what subject.” He forces himself to say.

“It was nothing. The whole point of tonight was to get away from all that junk.”

“Still, I owe you one.”

Rory clinks her tongue. “Well, if you put it like that, there is one thing you could do.” Jess turns to her expectantly. “So, as you know, Paris and I were talking about school things today.”

Jess fakes a gasp. “I never would have expected you were talking about school things at school.”

She smacks him without once looking away from the road. “Would you let me finish?”

“Sorry, continue.”

“ _ Anyway, _ we were talking, and she said that since we’re president and vice president, it would look weird if we didn’t go to prom.”

Jess shrugs, not following. “But I thought she was going with Jamie.”

“Oh, she is. She just doesn’t want me to be a no show. And I was thinking, since you said you owe me-”

“No.” Jess cuts her off as soon as he understands where she’s going with this. “Nope, no way. I am not going to prom with you, that’s gross.”

“Please! I don’t want to be stuck third-wheeling it with Paris and Jamie. And it would just be as friends, obviously, so no grossness involved.” She slows down her speaking, glancing at him every chance she gets. “Please. It will be an hour and a half, two max. We can spend the whole time making fun of all the annoying, snooty kids. You love making fun of rich kids. And I hear they spike the punch with the  _ really _ good stuff, like top shelf stuff. And you already have a suit from when we went shopping-”

“You’re not going to stop talking until I say yes, aren’t you.” He interrupts her with a sigh.

“You know me, where you lack at speech, I excel. I can just go on and on and-”

“Jesus, fine. But just so you know, this ask is way bigger than what I owe you, so now it’s tipped to where  _ you _ owe  _ me.” _

“But-”

“No buts. Either you owe me, or it’s no deal.”

It’s Rory’s turn to sigh. “Fine. But since this is to partially to pay back what you owe me, what I owe you in the future has to be a small thing, like a free burger from Luke’s.”

“Deal.” That works for him, part of the perk of living above the diner is that he eats there for free anyway. He’ll just tell Caesar it’s for him, then will give it to Rory when he’s not looking.

00000000000000000000000

  
  


Luke is a mix of anxiety and dread. Why does Jimmy have to keep butting in like this? A part of Luke wants to open the letter now so he can prepare to do damage control for whatever Jimmy is about to put Jess through, but he knows he can’t do that. God, the timing couldn’t be worse. They haven’t talked about the break up since the very short recap that Jess gave him the day after the party where Jess claims to be fine, but Luke knows he took it pretty rough. Rory helped some, whatever it was she said to him the next morning seemed to do some good, but the kid still hasn’t been himself lately. He’s more withdrawn, only talking if spoken to, and spending most of his time either reading upstairs or working at the inn. Lorelai mentioned he asked not to be at the front desk, instead wanting jobs that require the least amount of facetime with guests.

On top of that, Lorelai further explained that Jess tried to argue against being valedictorian because he felt he didn’t earn it. Luke knows without a doubt that if anyone at that school deserves the title it’s Jess. He’s one of the smartest people he knows. Hell, he’s the only person he knows that reads more than Rory does, and faster too. He’s watched Jess read an entire book in one sitting, and that was in a span of a couple hours is all. 

When he first started working downstairs, he had complained to Luke that customers  _ made _ him write down their orders because they didn’t trust him to remember them all. Just to prove a point to Luke, he started scribbling jibberish on the orderpad to make the customer ‘happy’, and still got every order right in the process. The regulars trust him now to get everything right, after Luke talked them into giving Jess a chance with the promise of their meal on the house if something is wrong with their order. He hasn’t had to comp one meal. 

A small part of Luke wants to hide the letter and show it to Jess when he knows he’s leveled out a bit more emotionally, but that’s not an option either. Hiding important things is what led to Jess running away before, and Luke made a promise to be more honest about things like this.

Well, he better make a decision prompto, because he just heard the door downstairs open and shut, and loud footfalls up the stairs that signal Jess is home.

“Hey.” Luke greets his nephew from the kitchen table as he comes through the door.

Jess only grunts in greeting, making a beeline for his dresser to change. He pauses to pet his cat, giving Luke an opening.

“So, um, before you change, can you come over here for a minute?”

Jess stares at him suspiciously. “Why?”

“Don’t worry, you’re not on trial here. You got a piece of mail today that is… interesting to say the least.”

Jess stays where he is, hand absentmindedly scratching under his cat’s chin. “What’s that mean?”

Luke keeps himself from snapping. “Come over here and you’ll find out.”

Rolling his eyes, Jess does as he’s told for once, coming to the table, but not sitting. Luke wordlessly hands Jess the envelope, hoping he’s doing the right thing.

Emotions cross Jess’ face. First confusion, then realization as he figures out who it’s from, then even more confusion as he looks up at Luke. “Why would Jimmy send me something?”

Luke shrugs. “Only one way to find out.”

Swallowing, Jess sits down, holding the envelope so tight he leaves creases. “Part of me wants to rip this up and not look at a word he has to say, but the more morbidly curious part of me wants to know what he thinks is so important that he had to mail something to me after everything he did, or didn’t do in this case.”

“You don’t need to make a decision now, you can sleep on it.”

Jess nods, staring ahead at nothing. “Yeah, I think I’ll do that.”

“Whatever you do, just know you don’t owe him anything. Open it, don’t open it, hell you can burn it if you want. It’s all up to you.” Luke decides the best thing he can do is give Jess some space, so he gets up and pats Jess on the shoulder, squeezing lightly. “Night, kiddo.”

Luke feels Jess start to lean into him before he catches himself and pulls away, tossing the letter on the table and standing. He heads to his dresser like he originally planned. “Night.”

Luke lets Jess have the bathroom first, taking off his hat. Collapsing at the foot of his bed, he runs his hands through his hair, hoping everything will turn out okay and that he didn’t just make everything worse for Jess.


	2. The Wreck We Made

**Notes for the Chapter:**

> Apologies for the delay getting this out, but I really wanted to make sure the last scene was exactly how I wanted it. You'll understand once you get to the end ;)
> 
> Title from Bastille's Happier
> 
> Spotify playlist for this series found here: https://open.spotify.com/playlist/2LGH9yFl7bBLz2YWc0uHM5

“In the cold light of day we're a flame in the wind

Not the fire that we've begun

Every argument, every word we can't take back

'Cause with the all that has happened

I think that we both know the way that the story ends” -Happier, Bastille 

0000000000000000000000000

It’s been a week and Jess still hasn’t opened the letter. By this point, everyone is dying to know what’s in the envelope, but Jess keeps finding reasons to put off opening it. Using school, work, even Fran’s funeral as an excuse for why he doesn’t want to open it. It’s not because he’s scared, no, of course not. Why would he be scared to open some stupid letter from a stupid jerk that he unfortunately shares half of his dna from? Him being scared of what may or may not be written would mean that some tiny little part of him would have to care about Jimmy, and he doesn’t. He’s had one conversation with the guy, nothing to form any bonds over. So, no, not scared. Definitely not scared.

Jess shakes his head to lose that train of thought as soon as humanly possible. He has more pressing things to worry about, like how on top of going to Rory’s stupid prom, she’s begging him to take her to Stars Hollow High’s prom too. She just found out that Lane is allowed to go, and told him how the two have always dreamed of doing the prom thing together since they were ten. He had already bought the tickets before the whole thing with Oliver went south, and the tickets, as he was rudely told by the student store, are nonrefundable. He tried just giving her the ticket so she can go on her own, but she was quick to remind him that they wouldn’t let her in unless she was with a currently enrolled student of the school, i.e. him.

With first Rory, then Lane at school both giving him record breaking puppy dog eyes, he folded like a deck of cards. 

He takes the mail from Ralph downstairs, a now safe place for him to be since Luke got people to stop treating him like a charity case, and starts to sort it. Spotting one from the financial aid office, he dumps everything on the counter next to Taylor and grabs a knife to get it open.

“Excuse me!” Taylor sputters. “That is my knife you just took to use as a letter opener.”

“You’re eating chili. What possible use could you have with a butter knife?”

“None, obviously, but it’s the principle of the thing. You don’t just go around taking peoples cutlery without even so much as asking-”

Jess ignores him as he scans the letter. “Shit!”

“Now there is no need for that kind of language.”

“Not you!” Jess snaps at him.

Luke, who had made it no secret that he was listening to the two bicker, jumps in. “What’s wrong?” He notices the envelope, picking it up. “Hey, is that the thing that lets you know if you qualify for financial aid?”

“What?” Jess looks up. “Yeah, uh, I got it. Obviously. I just wrote my social security number down wrong. I’m gonna go call them now and get that fixed.” 

Taylor scolds him over proofreading and proper penmanship as he leaves, Luke surprisingly quiet.

Shutting the upstairs door and locking it, he gets his phone and dials the number on the paper, trying to keep his hands from shaking. It has to be a mistake. These types of things happen all the time. He’ll talk to someone and get it straightened out in no time, because there is  _ no way _ him of all people don’t qualify for financial aid. He has exactly seventy-three bucks and a cat to his name, financial aid was made for someone like him.

After waiting on hold for what feels like an hour, then being bounced around from department to department, he finally finishes his story for the third person and they say he’s in the right place and to hold as they look up his information.

Rolling his eyes, he debates the merits of just slamming his head against a wall as he is forced to listen to the terrible on-hold music for ten minutes.

_ “Are you still there?” _ A feminine voice clicks on.

“Yes. Now, do you see what I mean-”

_ “I’m sorry, but the information you received is correct.” She cuts him off. “According to our records, you don’t qualify for financial aid with us.” _

Jess takes a breath, pinching the bridge of his nose. “Then your records are wrong. I work in a diner making minimum wage and live in what used to be my grandfather’s tiny office with my uncle. How the hell do I not qualify for financial aid?”

_ “Our records show that you live with your adoptive father, a Lucas Danes?” _

“Yeah, he’s my uncle, but he adopted me when I was seventeen. What does that have to do with anything?”

_ “Well, it says here that he owns two buildings and has two forms of income exceeding twenty-five thousand grand a year. Is this correct?” _

Jess switches the phone to his other hand as he uses his free one to run it through his hair, getting more and more impatient. “I don’t know, probably. None of that matters though because he’s not the one going, I am, and I’m not going to be living with him when I go to school. The only income that matters is mine, and I make virtually squat.”

_ “I’m sorry, but until you reach the age of twenty-six, financial aid is decided by the income of the father or your primary caregiver since you are still a dependent.” _

“That’s bullshit! Luke isn’t paying for a damn thing! Even if he was, there is no way in hell he could afford to put me through school for four years  _ and _ be able to keep his diner open!”

_ “Sir, I’m going to have to ask you to calm down-” _

“Screw calming down! I need that financial aid if-”

Dial tone cuts him off as the lady hangs up on him. Scoffing, he tosses his phone down on the table after snapping it shut. Before he can sit down, a knock comes from the door and he sees Rory’s silhouette through the frosted glass. With a groan, he throws the door open mid second knock.

“What?” He snaps.

Rory lowers her hand, shuffling in place. “I heard yelling. If this is a bad time, I can-”

Opening the door wider, he motions for her to come in. “Close the door behind you. And this time I’m serious,  _ no one _ can know about this, especially Luke.” He collapses in a chair at the table like he was about to before she interrupted.

She hesitates before nodding, doing as he said and sitting across from him. “So, what-” Not in the mood to talk, he just slides the letter over for her to read herself. She figures out the problem quickly. “This has to be a mistake, have you tried-”

“Calling them? You heard the tailend of my attempt at that. Apparently, Luke makes too much for me to qualify for financial aid.”

“What? That’s ridiculous.”

“It’s what it is apparently. They won’t count me as independent until I’m twenty-six.”

“Jess, this is crazy, you have to tell Luke.”

“I’m not planning on keeping it a secret forever, I just need some time to think about what I’m going to do next before he tries to jump in and fix everything himself. I’ve told you before and I’m sticking with it that he is not going to pay a dime.”

Rory goes silent, fiddling with the paper. “You’re still gonna go, right? I was really looking forward to us being at the same school together and I know it won’t be the same if it’s just me.”

“What? Now who’s being crazy? After all this work you made me put into this crap, I don’t care if I have to sneak into every class, I am going to that damn school.”

Rory smiles at him, relief clear on her face. “Thank you.”

Jess feels his face heat up, and he snatches the paper back so he can hide it somewhere in his room where Luke won’t find it. If that means he doesn’t have to look at her, then that’s just an added bonus.

“Anyway, onto a more cheery subject, Stars Hollow’s prom is in two weeks. I’ve talked to Dave, who relayed to Lane during one of their ten minute phone talks that we are going to meet them at my place so Mom can get all her photo taking out of her system.”

Jess rolls his eyes, sitting back down. “Great, there’ll be photographic proof of this evening.”

Rory shoots him a mock glare. “Oh, shush you, or I won’t help you with your speech.”

“Then I won’t help you study for your math final.”

“Then we’ll both look like fools.” Glancing at her watch, Rory stands. “I need to get going. Promise me you’ll get help from someone before you do something stupid like get student loans that will follow you for the rest of your life.”

Jess rolls his eyes, scoffing. He stands as well to show her out. “I’m crafty. I’ll figure something out.”

She stops, pointing at him. “Something legal. I’m not going to visit you if you get caught robbing a bank.”

Jess snaps his fingers. “Damn. Back to the drawing board for me.”

She sends him a ‘I’m watching you’ gesture as she heads out, Jess shutting the door behind her. Now that he’s alone, Billy crawls out from his hiding place, trotting up to him. Jess picks him up, which earns him a pur.

“Hey, buddy, you wouldn’t happen to have thirty grand laying around anywhere, would you?”

He lets out a single meow, taking his paw and lightly bating at Jess.

“Yeah, that’s what I thought. You know, we’ve been meaning to talk, and I think you really need to start pulling your weight. Once we’re at Yale you won’t have grandpa Luke around taking pity on you and giving you free tuna all the time. Maybe you should stop with the sad eyes on him and start sending them toward the financial aid office.”

Billy meows at him two more times and Jess nods understandingly.

“Yeah, you’re probably right. If they spend all day denying kids their future, they will be immune to your begging look too.”

0000000000000000000000

Due to Rory’s crazy, hectic study schedule that he got sucked into, and her lack of a car while Lorelai is stuck running the grad night booth at Chilton, he has to pick Rory up from Hartford. Luckily she walked to Emily and Richard’s since Emily wanted her to ‘bring a swatch of her gown so she won’t clash at graduation’. He’s just glad he can avoid Chilton. He knows the chances of seeing Oliver there are slim, it is a large school, but with his crappy luck they would end up running into each other anyway.

The upcoming finals and graduation have been a welcome distraction, and everyone from Luke to Mrs. Kim have told him that it will get easier with time, but that time can’t come any quicker. When he lets himself stop, even for a moment, his heart feels like sinking and he hates that he opened himself up to love. And that’s what it was too. 

Love.

He’s such a fool for letting someone in that isn’t family for the first time and letting them hurt him like this. Sure, he loves Lorelai, Rory, and Luke, but that paled in comparison to what he was starting to feel for Oliver. Now it was all thrown back at him and he’s left with this hole that can’t seem to be filled no matter what he does or who he spends time with. He’ll plaster on a smile and they all think he’s doing better, moving on with his life, but he knows. Times like this when he’s alone in a car for forty minutes he knows the truth. A part of him is stuck and he doesn’t know how to get unstuck, to move forward with his life.

Typing in the code for the driveway, he forces his smile back on as he parks the truck and goes to the door to get Rory. Less than a second after he rings the doorbell, Rory appears.

“Whoa, where’s the fire?” He asks in shock as she tries to turn him around.

“Tell you later, let’s go.”

“Rory? Who is that at the door?” Emily asks from inside. She comes around the corner behind Rory in a fancy dress. “Jess, this is a pleasant surprise. Please, come in.”

“Sure…” Glancing at Rory, who mouths an apology before moving aside.

Emily leads him into the living room, which has turned into a fashion show with all the racks of clothes around. An older lady is there, holding up swatches to Richard. “Miss Celine, I’d like you to meet our grandson Jess-”

Miss Celine gasps, dropping the swatches into Richard’s hands. “Emily, you didn’t tell me Prince Charles was coming to visit. Richard, isn’t he just the spitting image of Prince Charles on his wedding day with Lady Diana?”

Richard hums, looking him up and down. “Now that you mention it, if he only got a haircut-” He says teasingly, knowing Jess likes it on the longer side.

His face heats up. “My hair is fine the way it is. I’m just here to pick Rory up.”

Miss Celine comes up to him, brushing his hair out of his face so she can get a better look at him. “You know, Your Highness, I helped the late princess pick out her dress. I warned her, I said, ‘Diana, be careful around that Charles, he has his eyes set on another.’. Poor girl would still be alive if she had taken my advice. But you’re not like that chad Charles, are you?” Miss Celine pauses, staring at him so intently it feels like she’s looking into his soul. He jumps in surprise when she pats him on the cheek. “Please, sit Your Highness, help Sabrina here pick out your grandparents’ outfits for your guys’ big day.”

Jess finds himself being sat on the couch next to Rory. “I tried to warn you.” She whispers to him while everyone is distracted.

“Sabrina?” He asks instead, trying to think of every famous person named Sabrina that Rory could maybe, sorta look like.

Rory rolls her eyes. “Audrey Hepburn from  _ Sabrina.” _

Jess nods. “Yeah, I could see that. If I squint and tilt my head to the side, I could definitely see it.”

She holds back a laugh, trying to look serious as she elbows him. “Whatever you say, ‘Your Highness’.”

“Rory, Jess, pay attention.” Emily snaps at them.

“Yes, ma’am.” They both say looking up, pushing their laughter down.

000000000000000000000000

After two hours of the ridiculousness, Jess excuses himself to ‘use the bathroom’, calling Lorelai so she can set them free. Things get… awkward to say the least between Emily and Lorelai once she arrives. He was hoping their little feud had blown over by now, especially since Lorelai is actually trying to make conversation, but Jess can see where Lorelai and Rory got their stubborness from. Jess and Rory sit quietly on the couch, watching the mother and daughter duo argue about dinner times and Emily making up excuses about dinner not being ready, despite everyone able to smell it.

Richard, oblivious to the tension in the room, comes in wondering where dinner is. Lorelai calls Emily on her bluff about having plans, throwing him and Rory under the bus by saying they are staying for dinner. Richard is thrilled, heading into the dining room.

With a few last biting words, Lorelai storms out, Rory chasing after her. Not sure what to do, Jess stays on the couch, watching Emily gather up the reject gowns that are draped over the chairs. A moment later, Rory comes stomping back in, shoving her books in her bag. At the forty-five minute mark, she had decided if they were stuck here, they might as well get some studying done.

“Are you staying?” Emily asks.

“No, Grandma, I have to go.” Rory answers, not looking up from her bag.

“Alright, I guess we’ll see you at graduation, then.”

“I guess you will.” Rory snaps. Oh, no, she’s in one of her very pissed off moods. If Emily knows better, she’d abort right about now.

“I swear,” She starts again. Well, this isn’t going to end well. “I don’t know what to do with that mother of yours, I really don’t. Everything has to be  _ such _ a scene.”

Rory glares at her. “I think you’re being really stupid.” There it is.

With that said, Rory leaves for good, missing the look of shock that passes Emily’s face. It’s gone as quickly as it appeared as Emily remembers he’s still there. “What was that all about?” She asks him, gesturing to where Rory was.

“Was it worth it?” He asks instead.

“Was what worth it?” She plays dumb, going back to collecting the clothes.

Shaking his head, he gets up, shrugging his jacket on. “If it’s all the same to you, I’m gonna pass on the burnt dinner. You might want to order a pizza instead.”

Getting his point across, he leaves as well, finding Rory and Lorelai still outside sitting in the jeep. Lorelai rolls down her window. “Souplantation? My treat.”

While not his favorite, he’s not one to turn down a free meal. He shrugs. “Sure, why not.”

Lorelai grins. “Great, we’ll meet you there.” Not waiting for him, she heads out, reversing out of the driveway with a wave.

About to get in the truck, he stops when the front door opens and Richard calls out for him to wait. Not having any sort of beef with him, aside from the slight jab about his hair earlier, he meets him halfway. He feels a little bad ditching without any sort of goodbye, but there was no way he wanted to be alone for a whole dinner after everything that happened with Lorelai and Rory.

“Heading out so soon?”

Jess winces, nodding. “Yeah, sorry. Things just got a little too much.”

Richard chuckles unexpectedly. “I don’t blame you. We seem to have gotten the short end of the stick when it comes to this little tiff between Lorelai and Emily. I’m sure the two will work it out soon enough, but for the time being, I wanted to give you this.” He hands him a small box he had been holding. Opening it up, Jess finds a deep blue bowtie. “I had noticed at Sookie’s wedding last year that you didn’t seem too fond of the tie you were wearing, so I thought this might be a little more suited for you to wear to your prom. It’s cotton, so a little more informal which I know is more your taste, and since it’s not hanging you won’t have to worry about it getting caught on something.”

“Thank you.” Jess says softly, staring at the bowtie. He’s surprised Richard picked up on all that back then. They barely knew each other at the wedding, just occupying the same space as they read their books in silence at the reception. He never told Luke, mostly out of embarrassment, but the main reason he didn’t want to wear a tie before was because he didn’t like how it hangs around your neck where anyone could grab it. Bowties are different though, now that he thinks about it. Where when you pull a tie, it only gets tighter, but a bowtie will just come undone and can’t hurt you. Looking up at Richard, he thanks him again. “Seriously, thanks. Despite what people think, maybe they aren’t so dorky.”

Richard mock gasps, straightening his own bowtie. “Who says that? Bowties are cool.”

Jess snorts. “Whatever you say. I’ll see you later.”

Richard smiles and nods, telling him to have a good night before heading back inside.

Jess looks at the bowtie one last time before shutting the box and heading to his truck. He better hurry before the Gilmore girls eat everything at the buffet.

000000000000000000000

The Stars Hollow prom ended up not being as bad as he thought it would be. The worst part, as he expected, was before at Lorelai’s when they got all the pictures taken. Luke and Lorelai would not quit fussing over him, making him comb his hair to the side ‘the right way’ and straightening his bowtie about a hundred times. They both thought it was  _ cute _ that Richard had given it to him. Lorelai went as far as making Rory a dress that matches it. Jess didn’t think it was possible to make a dress in two weeks, but Lorelai waved him off and said that she’s had a lot of time on her hands since business at the inn has been so slow. Once Lane and Dave arrived, Lorelai took about a rolls worth of pictures until Luke took pity on everyone and got her to stop, telling them to escape while they have the chance.

The prom itself was pretty boring. The school was too cheap to rent a hall from any hotels, so they just had it in the gym. It worked in his favor though, because he was able to sneak off to get a book from the library. The only adult he made friends with at the school was the librarian, who gave him a key months ago. He got a book and returned to the gym in less than ten minutes, Rory being the only one who even noticed he left. 

She comes over to where he’s been leaning against a wall when a slow song comes on, giving Lane and Dave some privacy. “I thought Luke didn’t let you bring a book.” Noticing it’s one from the school library, she rolls her eyes. “Please say you got that from your locker.”

“I got it from my locker.” He parrots back with a slight smirk.

“Liar.”

“Relax, I’ll return it before the night is over.”

Rory eyes him one more time before leaving him be and heading over to the punch table, which has remained sadly unspiked the whole night. Seriously, what kind of school doesn’t have a spiked punch bowl. Losers.

Dean was there with Lindsay, so he wisely kept his distance, only talking to him shortly while Lindsay went to the bathroom with some friends. Jess was on Rory’s side when it came to the news that Dean proposed to her, but kept his opinion on the boneheaded move to himself. Dean was there for him after his break up with Oliver, and the last thing he wants to do is push away one of the few rocks he has.

As he was sure would be the case, he didn’t win prom king. Some jock won instead, but he doesn’t know who he is. That was a relief, since the last thing he wanted was to win prom king on top of the stupid valedictorian thing. Once word about that started to spread around the school, everyone’s been congratulating him like they were old friends when in reality most of them hated him when he first moved here.

The prom ended soon after that, and as promised Jess returned the book he had borrowed from the library. Doing the gentlemanly thing, he walks Rory back to her place, listening to her talk about how much fun she had with Lane.

“Seriously, Jess, thank you so much for this. This was one of the best nights of my life.” She tells him for the fifth time as they stop in her front yard.

He waves her off. “It was nothing. The tickets were already paid for and would have just been wasted sitting in my dresser.”

“Still, I know you would have rather gone with Oliver than someone who is basically your sister-”

“Stop that, you know I’d pick you any day of the week.”

Rory shakes her head. “You don’t mean that.”

“Of course I do. Relationships come and go, but you’re my best friend. Even if I was still dating him, had I known you wanted to go to the Stars Hollow prom I would have taken you. I would’ve just gone to the Chilton one with him.”

She looks at him like he hung the moon. “Thank you.”

He shifts in place, suddenly embarrassed at the mushy turn this conversation took. “Yeah, well, whatever. Someone had to go with a dork like you.”

She smirks at him, letting the conversation shift to something he’s more comfortable with. “Says the nerd who was reading at prom.”

“You’re just jealous you didn’t think to bring a book.”

“Whatever you say, nerd. Night.” She gives him a quick hug before shoving him in the direction of Luke’s.

He waves goodbye. “See you next week to do this whole song and dance again.”

000000000000000000000000

A week passes by too quickly for Jess’ liking, and he finds himself on the way to Rory’s prom now. By an unspoken agreement that Jess is definitely going to be drinking the spiked punch, Rory drives them in her mom’s jeep. They get there extremely early, per Paris’ instructions, to help oversee the set up.

Jess openly gawks at the literal mansion in front of them, thinking how completely different this prom is to the lame one his school threw in the gym. “Damn, this place makes Emily and Richard’s place look small.”

Rory looks over her shoulder at him, not noticing he stopped. “Huh? Oh yeah, I guess it is pretty big. I’ve seen it so many times with Paris I guess the novelty wore off for me. It’s not like we get the entire building either, just the downstairs where the ballroom is. C’mon, I can hear Paris terrorizing the setup crew from here.”

Shaking his head, Jess sticks his hands in his pockets and follows after her. A valet crew is setting up outside the doors and pause to greet him and Rory. She says hello and waves, while he just nods in greeting.

The inside is just as pristine as the outside, flower vases lining the walls and nice paintings all around. He doesn’t know much about fancy artwork, but he’s pretty sure just one of the paintings could pay for his college tuition three times over.

Rory expertly leads them through the winding halls until they find the ballroom, where Paris is harassing the band trying to warm up. Jamie spots them first and sends Rory a ‘please help’ look. With a sigh, Rory rushes over, smoothing things over between Paris and the band. Not wanting to get caught in the middle of that, he wanders over to Jamie. He’s only met the guy a handful of times, but between Rory’s stories from DC and his own experiences with him, he gets the overall impression that he is just a normal, nice guy. A little too normal to want to be with Paris of all people, but to each their own he guesses.

“What did they do to set her off?” He asks with his voice low enough that Paris won’t overhear him.

“The guitarist was out of beat with everyone else. Said it was so bad, a deaf person can tell he was off beat.” Jamie whispers back.

“Well, for that he should be taken out back and shot.”

Jamie snorts, shaking his head. “Thank God Rory arrived when she did, or Paris may have gone through with that. She is the only one Paris will listen to.”

Jess smirks at that, not denying it. They drop the conversation as Rory leads Paris over to them and away from the band with an apology before they quit on the spot.

Paris looks him up and down, shock evident on her face. "Look at that, you do clean up."

Jess gives her a sarcastic grin. "It's like they say, miracles happen every day."

Jess hangs back the rest of the time as people slowly start to trickle in. Since Rory said they had the whole downstairs of the mansion, he spends his time away from the ballroom once it gets a little too crowded for his tastes, exploring the other rooms. He had gotten a glass of punch earlier, but unfortunately it was before anyone was around to spike it. He’ll make his way back eventually, but for now he’s enjoying sitting on the steps outside that lead down to the back garden with one of the last cigarettes he had smuggled away a while back.

The sun had set about an hour ago, leaving the grounds dark except for the light from inside flooding out. He can hear the vague sounds of the band playing inside, but it’s too muffled to make out any particular song. This is the first time he’s felt any sort of calm for weeks now, and he really doesn’t want it to end.

It does though, because everything he enjoys does, when the back door opens and shuts. He turns to see who it is, snuffing out his cigarette in case it’s one of the chaperones as he does. He squints, only able to make out the silhouette of a person from the bright lights inside. He can tell it’s one of the students and not an adult, but that’s about it. Damn, he had only just started smoking that cigarette too.

They freeze as soon as they spot him. “I’m sorry, I didn’t know anyone was out here- oh.”

Jess forces himself to stay calm as he hears a very familiar voice. One he didn’t think he would hear tonight. Keeping his voice even, he nods. “Hey, Ollie. Of all the gin joints in all the world.”

Oliver makes his way over to him hesitantly, gripping his own glass of punch tightly. Jess is slightly relieved that he’s not the only one feeling the intense awkwardness of the situation. “Are you, um… here with Rory?”

Jess rolls his eyes, facing forward again and taking a sip of his punch, wishing it was more than just punch. “I’m certainly not here with Paris.” It comes out more biting than he means for it to, but he can’t help the irritation gnawing at the pit of his stomach. He’s been sad and depressed about their breakup for weeks, but now that Oliver is in front of him he just feels anger. Did he really move on so easily that he thinks Jess did too? That he was able to put all they had aside so quickly and go to prom with an actual date? Now that Jess thinks about it, he obviously did if he’s here.

Oliver flinches at his harsh tone. “No, of course, I was just curious. I’m here with a group of friends from school and-”

“What are you doing, man?” Jess cuts him off, not able to listen to him ramble on anymore.

“Just… trying to talk to you.” He answers meekly.

“Why?” He demands, glaring at him. “In case you forgot,  _ you _ broke up with  _ me.” _

Oliver starts and stops a few times. “I… I mean- I just- I-” Tears build up in his eyes and quickly make their escape. He bites his lip and tries to brush them away with the hand not currently holding his punch, but they’re coming too fast for him to keep up.

With a sigh, Jess’ anger melts away and is replaced with guilt for causing him to cry. “Hey. Hey, c’mon, calm down. Sit down before you fall down.” With a tap of his leg to get his attention and slight tug, Oliver crumbles onto the step next to him. Taking his drink before he spills it, he puts the punch to the side and out of the way. “C’mere, you’re alright, just breathe, okay? You’re going to be fine.” He collapses into him with a gasp as fresh tears start again, which Jess allows without thinking and holds him tight, running a hand up and down his arm. 

Oliver buries his face into his neck, holding the back of his jacket in a vice grip. “I’m so, so, sorry! All you did was try and help me that night, and I was a horrible jerk to you, calling you all those names! I was mean, and cruel, and, and-” He cuts himself off with a hiccup, crying even harder to the point where words can’t escape.

Jess shushes him, rocking slightly and resting his cheek on top of his head. “Hey, don’t say that, you’re not any of those things.”

“I’m a terrible person!”

“You are not a terrible person.”

Jess continues to hold him for the next couple minutes until his crying finally starts to slow down. Oliver sniffs, loosening his grip on his jacket, but not making a move to pull back. Jess doesn’t push it, closing his eyes and trying to commit his scent to memory. “I miss you so much.” Oliver mummers so softly into his jacket that he barely hears it.

“I miss you too.” Planting a lingering kiss on top of his head, Jess forces himself to pull back. Oliver pulls back as well, wiping the last of his tears from his red eyes.

Oliver sniffs again, voice still shaky. “I feel a ‘but’ coming on.”

Jess sighs, wishing he didn’t have to do what he’s about to, but he needs to say it, for both of their sakes. “You were the first person I could truly see spending the rest of my life with, and it scares the hell out of me that I still feel that way, but when we fight,” Jess shakes head, shutting his eyes for a moment and then opening them again to look Oliver in the eye. “When we fight, we hold  _ nothing _ back. We go for killing blows. And we don’t deserve that. Neither of us do.” Jess pauses, letting it sink in. “The things I said to you in New York, and the things you said to me at that party… We were trying to hurt each other, and that’s not healthy.”

Oliver nods, swallowing. “You’re right. You’re completely right. I really hate it, but you’re right.”

Jess can feel his own tears start to build up behind his eyes, and tries his hardest to keep them from falling. “I’m sorry, I wish we could go back and fix this, but…”

Oliver cups his cheek, using his thumb to wipe away a stray tear that escaped. “I know, I understand.”

Jess sniffs and grips his hand to keep it in place for just a little longer, turning slightly so he can kiss his palm.

Oliver leans in slowly, slow enough that Jess could pull back at any time, but instead he meets him halfway, closing his eyes and putting everything he has into what he knows is their last kiss. When they need to breathe, they only pull back just enough, resting their foreheads together to prolong the inevitable. “I will always love you, no matter what.” Oliver whispers.

Jess tries to say it back, but the words get stuck in his throat. He opens his eyes and tries to convey it that way instead.

He must understand, because he nods with a watery smile and gives him one more short kiss before pulling back for good. Jess lets his hand slip out of his own, leaving a cold spot where his hand had been resting on his cheek the whole time.

Clearing his throat, Oliver grabs his forgotten punch. One sip and he makes a face, coughing and sputtering, which effectively ruins the moment. Jess lets out an unexpected laugh at the timing. With a small apology, Jess grabs his own punch, holding it out. “Switch? I got it pre-spiking.”

Oliver nods, holding his out to Jess and pounding his chest, trying to clear his throat. “Thanks.” He croaks, taking a few small sips to chase down the strong alcohol.

Jess takes a test sip, shocked at the strong burn and has to clear his own throat. “Wow, Rory wasn’t kidding when she said they spike it with the good stuff.”

Oliver chuckles, glancing at the door. “My friends are probably wondering where I am. I should, uh…”

Jess nods. “Right, I abandoned Rory awhile ago and should find her pretty soon.”

Oliver stands, brushing the seat of his pants and then grabbing his drink off the ground. He hesitates before he leaves though. “I hope you have a really great life.” He says.

“I hope you do as well.” Jess says and finds himself meaning.

“Goodbye, Jess.”

“Bye, Ollie.”

They give each other a bittersweet smile before Oliver leaves for good. Jess keeps his eyes firmly locked on him until the door clicks shut behind him, then lets his smile drop. All the emotions he had been holding back come rushing in all at once. He gasps, covering his mouth to stiffen his sobs and lets his tears fall freely.

This is how Rory finds him some time later, still crying on the steps like some stupid baby. She doesn’t say anything, just comes over and sits next to him, hugging him tight. He leans into her, trying to stop crying long enough so he can speak. “I really wanna go h-home now.” He manages to get out.

He feels Rory nod and she tightens her hold on him. “Okay. Whatever you want.”

**Notes for the Chapter:**

> Don't worry, this isn't the last you'll see of Oliver. Like the Terminator, he'll be back.

**Author's Note:**

> Tumblr is Pineapplem00n, and don't forget to check out the spotify playlist I have for this series here https://open.spotify.com/playlist/2LGH9yFl7bBLz2YWc0uHM5


End file.
